Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Anti-oxidative and Antibacterial Constituents from Sedum hybridum

  • Gendaram, Odontuya (Natural Product Chemistry Laboratory, Institute of Chemistry and Chemical Technology, Mongolian Academy of Sciences) ;
  • Choi, Yoen-Hee (Phytochemistry Laboratory, Korea Research Institute of Chemical Technology) ;
  • Kim, Young-Sup (Phytochemistry Laboratory, Korea Research Institute of Chemical Technology) ;
  • Ryu, Shi-Yong (Phytochemistry Laboratory, Korea Research Institute of Chemical Technology)
  • Received : 2011.10.25
  • Accepted : 2011.12.02
  • Published : 2011.12.30
Download PDF
⟨ Previous Next ⟩

Abstract

Phytochemical studies on the whole extract of Sedum hybridum L., a Mongolian medicinal plant, has been undertaken to isolate active principles responsible for its anti-oxidative and antibacterial activities. Eighteen known compounds, i.e. (1) quercetin, (2) kaempferol, (3) herbacetin-8-O-${\beta}$-D-xylopyranoside, (4) myricetin, (5) gossypetin-8-O-${\beta}$-D-xylopyranoside, (6) gallic acid, (7) 2,4,6-tri-O-galloyl-D-glucopyranose, (8) 6-O-galloylarbutin, (9) myricetin-3-O-${\alpha}$-L-arabinofuranoside, (10) quercetin-3-O-${\alpha}$-L-arabinofuranoside, (11) caffeic acid, (12) ethylgallate, (13) (-) epigallocatechin-3-O-gallate, (14) palmitic acid, (15) stearic acid, (16) stearic acid ethyl ether, (17) ${\beta}$-sitosterol and (18) ${\beta}$-sitosteryl-O-${\beta}$-D-glucopyranose have been isolated and their molecular structures identified by spectroscopic analysis. Thirteen substances including seven flavonol components (1, 2, 3, 4, 5, 9 and 10), five gallic acid derivatives (6, 7, 8, 12 and 13) and caffeic acid (11) exhibited significant, dose-dependent, DPPH radical scavenging activity. Galloyl esters 12 and 13 were revealed to be main active principles for the antibacterial property of the extract of Sedum hybridum L.

Keywords

References

  1. Agrawal, PK. and Rastogi, R.P., $^{13}C$ NMR spectroscopy of flavonoids. Heterocycyles 16, 2181-2236 (1981). https://doi.org/10.3987/R-1981-12-2181
  2. Ahmad, F, Ali, M., and Alam, P., New phytoconstituents from the stem bark of Tinospora cordifolia Miers. Nat. Prod .Res. 10, 926-934 (2010).
  3. Budancev, A.L., Plant resources of Russia. Flowering wild plants, their phytochemical constituents and biological activities. Family Crassulaceae. KMK press: Saint Peterburg. V2, 200-206 (2009).
  4. Bus, J., Sies, I., and Lie, K.J. $^{13}C$ NMR of methyl, methylene and carbonyl carbon atoms of methyl alkenoates and alkynoates. Chem. Phys. Lipids 17, 501-518 (1976). https://doi.org/10.1016/0009-3084(76)90049-9
  5. Cui ChB, Tezuka Ya, Kikuchi, T., Nakano, H., Tamaoki, T., and Park, J.H., Constituents of a Fern, Davallia mariesii Moore. I. Isolation and structures of davallialactone and a new flavanone glucuronide. Chem. Pharm. Bull. 12, 3218-3225 (1990).
  6. Chen Xin-Min, Yoshida T, Hatano Ts, Fukushima, M., and Okuda, T., Galloylarbutin and other polyphenols from Bergenia purpurascens. Phytochemistry 2, 515-517 (1987).
  7. Cowan, M.M., Plant products as antimicrobial agents. Clin. Microbiol. Rev. 4, 565-592 (1999).
  8. Enkhmaa, G., Sarnaizul, E., Ouyntsetseg, T., Sukhkhuu, B., Odontuya, G., Kim, Y.S., and Ryu, S.Y. Antimicrobial activity of Mongolian medicinal plants. Nat. Prod. Sci. 14, 32-36 (2008).
  9. Grubov, V.I., Key for vascular plants of Mongolia. Nauka press: Leningrad, 133-134 (1982).
  10. Gunstone, F.D., Pollard, M.R., Scrimgeour, C.M., Gilman, N.W., and Holland, B.C., $^{13}C$ Nuclear magnetic resonance studies of acetylenic acids. Chem. Phys. Lipids 17, 1-13 (1976). https://doi.org/10.1016/0009-3084(76)90031-1
  11. Haslam, E., Natural polyphenols (vegetable tannins) as drugs: Possible modes of action. J. Nat. Prod. 59, 205-215 (1996) https://doi.org/10.1021/np960040+
  12. Harborne, J.B., The flavonoids, Advances in research since 1986. Chapman and Hall: London, 448-496 (1994).
  13. Karaman, I., Sahin, F., Guluce, M., Ogutcu, H., Sengul, M., and Adiguzel, A., Antimicrobial activity of aqueous and methanol extracts of Juniperus oxycedrus L. J Ethnopharmacol 85, 231-235 (2003). https://doi.org/10.1016/S0378-8741(03)00006-0
  14. Khaidav Ts and Agafanova, T., Curative preparations of folk medicine, Mongolia. State press: Ulaanbaatar, 12, 24-25 (1969).
  15. Khaidav Ts and Menshikova, T.A., Medicinal plants in Mongolian medicine. State press: Ulaanbaatar, 192 (1978).
  16. Knothe, G. and Kenar, J.A., Determination of the fatty acid profile by $^1H$ NMR spectroscopy. Eur. J. Lipid Sci. Technol. 106, 88-96 (2004) https://doi.org/10.1002/ejlt.200300880
  17. Kurkin, V.A., Zapesochnaya, G.G., and Shchavlinskii, A.N., Flavonoids from aerial parts of Rhodiola rosea. Khimiya Prirodnykh Soedinenii 5, 657-658 (1984).
  18. Ligaa, U., Medicinal plants of Mongolia used in western and eastern medicine. JKC printing: Ulaanbaatar, 241-244 (2006).
  19. Markham, K.R., Ternai, B., Stanley, R., Geiger, H., and Mabry, T.J., Carbon-13 NMR studies of flavonoids - III. Tetrahedron 34, 1389-1397 (1978). https://doi.org/10.1016/0040-4020(78)88336-7
  20. Mensor, L.L., Menezes, F.S., Leitao, G.G., Reis, A.S., Santos, T.C., Coude, C.S., and Leitao, S.G., Screening of Brazilian plant extracts for antioxidant activity by use of DPPH free radical method. Phytother. Res. 15, 127-130 (1978.)
  21. Pietta, PG., Flavonoids as antioxidants. J. Nat. Prod. 63: 1035-1042 (2000). https://doi.org/10.1021/np9904509
  22. Rice-Evans, C.A., Miller, N.J., and Paganga, G., Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Rad. Biol. & Med. 7, 933-956 (1996).
  23. Sakar, M.K., Petereit, F., and Nahrstedt, A., Two phrologlucinol glucosides, flavan gallates and flavonol glycosides from Sedum sediforme flowers. Phytochemistry 1, 171-174 (1993).
  24. Sato Yo, Oketani, H., Singyouchi, K., Ohtsubo, T., Kihara, M., Shibata, H., and Higuti, T., Extraction and purification of effective antimicrobial constituents of Terminalia chebula Rets. against meticillin resistant Staphylococcus aureus. Biol. Pharm. Bull. 4, 401-404 (1997).
  25. Sviridinov, G., Useful plants of Gornogo Altaiya. Press: Gorno-Altaisk, 231 (1978).
  26. Tuong, P.T., Kang, H.J., Na, M.K., Jin, W.Y., Youn, U.J., Seong, Y.H., Song, K.S., Min, B.S., Bae, KHw., Anti-oxidant constituents from Sedum takesimense. Phytochemistry 14, 2015-2022 (2007).
  27. Usuki, S., Ariga, T., Dasgupta, S., Kasama, T., Morikawa, K., Nonaka, Sh, Okuhara, Ya, Kise, M., Yu, R.K., Structural analysis of novel bioactive acylated steryl glucosides in pre-germinated brown rice bran. J. Lipid Res. 49, 2188-2196 (2008). https://doi.org/10.1194/jlr.M800257-JLR200
  28. Yasukawa, K., Ogawa, H., and Takido, M., Two flavovonol glycosides from Lysimachia nummularia. Phytochemistry 5, 1707-1708 (1990).